Lawesson's reagent → HCID 87889787, compound

HRID 1796030Notes

Reaction equation

HRID 1796030 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]([F:38])([F:37])[C:25]1[CH:30]=[CH:29][N:28]2[C:31]([C:34]([NH2:36])=O)=[CH:32][N:33]=[C:27]2[N:26]=1>C1(C)C=CC=CC=1>[F:23][C:24]([F:38])([F:37])[C:25]1[CH:30]=[CH:29][N:28]2[C:31]([C:34](=[S:10])[NH2:36])=[CH:32][N:33]=[C:27]2[N:26]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 69560089HCID 69560089, compound

Product 1

HCID 87889787HCID 87889787, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (281 mg, 0.7 mmol) was added to a stirred suspension of the foregoing amide (160 mg, 0.7 mmol) in toluene (16 ml). The resulting mixture was heated at reflux for 2.5 h and then concentrated under reduced pressure while dry loading onto silica. Subsequent purification by column chromatography on silica using firstly diethyl ether and then EtOAc/ether gave 7-trifluoromethylimidazo[1,2-α]pyrimidine-3-carbothioamide (160 mg, 93%): δH (360 MHz, d6-DMSO) δ 7.80 (1H, d, J 7.2), 8.70 (1H, s), 9.73 (1H, s), 9.82 (1H, s), 10.87 (1H, d, J 7.2).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2.5 h
  3. concentrationconcentrated under reduced pressure
  4. customwhile dry loading onto silica
  5. customSubsequent purification by column chromatography on silica using firstly diethyl ether

Sources & evidence

ORD record
ord-4d34201062d6499ba3e68d6243e29c08
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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